Literature DB >> 31290674

Palladium-Catalyzed Suzuki-Miyaura Reactions of Aspartic Acid Derived Phenyl Esters.

Amira H Dardir1, Nilay Hazari1, Scott J Miller1, Christopher R Shugrue1.   

Abstract

Transition-metal-catalyzed transformations of amino acids and peptides could provide a powerful method for their site-selective modification. Here, we report non-decarbonylative Pd-catalyzed Suzuki-Miyaura reactions of phenyl ester derivatives of aspartic acid to form aryl-amino ketones. These products are potentially important in the synthesis of pharmaceuticals, and our methodology represents a new route to access molecules of this type.

Entities:  

Year:  2019        PMID: 31290674      PMCID: PMC6939165          DOI: 10.1021/acs.orglett.9b02214

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  36 in total

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Review 4.  Strategic approaches to optimizing peptide ADME properties.

Authors:  Li Di
Journal:  AAPS J       Date:  2014-11-04       Impact factor: 4.009

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Authors:  Anaïs F M Noisier; Margaret A Brimble
Journal:  Chem Rev       Date:  2014-08-21       Impact factor: 60.622

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Journal:  Pept Res       Date:  1988 Sep-Oct

7.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

8.  Bupropion slow-release response in depression: diagnosis and biochemistry.

Authors:  P J Goodnick; R A Dominguez; C L DeVane; C L Bowden
Journal:  Biol Psychiatry       Date:  1998-10-01       Impact factor: 13.382

9.  Organometallic palladium reagents for cysteine bioconjugation.

Authors:  Ekaterina V Vinogradova; Chi Zhang; Alexander M Spokoyny; Bradley L Pentelute; Stephen L Buchwald
Journal:  Nature       Date:  2015-10-29       Impact factor: 49.962

10.  Suzuki-Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C-N and C-O bonds.

Authors:  Peng Lei; Guangrong Meng; Shicheng Shi; Yun Ling; Jie An; Roman Szostak; Michal Szostak
Journal:  Chem Sci       Date:  2017-08-01       Impact factor: 9.825

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  2 in total

1.  Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters.

Authors:  Amira H Dardir; Irene Casademont-Reig; David Balcells; Jonathan D Ellefsen; Matthew R Espinosa; Nilay Hazari; Nicholas E Smith
Journal:  Organometallics       Date:  2021-05-27       Impact factor: 3.837

2.  Organometallic AlaM Reagents for Umpolung Peptide Diversification.

Authors:  Feng Zhu; Wyatt C Powell; Ruiheng Jing; Maciej A Walczak
Journal:  Chem Catal       Date:  2021-06-28
  2 in total

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